Olivia Rodrigo: The First Poshmark Pop Star
In her newest music video, Olivia Rodrigo dives into a Y2K vintage fashion fantasy, playing to the turn-of-the-millennia search term that is driving a craze of young shoppers to fashion resale platforms like eBay and Poshmark.
The video’s early 2000s style classics like Roberto Cavalli and Betsey Johnson dresses follows other recent notable vintage fashion moments for the singer, like wearing a ’90s pink Chanel suit for a publicity junket at the White House and various off-duty looks with worn-in T-shirts, nostalgic sunglasses and micro-mini kilts that could have been sourced from a local thrift store.
More from WWD
Call her the first Poshmark pop star. Rodrigo’s carefully crafted fashion sense — with its upcycled clothing, on-the-cusp designers and nonchalant styling — speak to her relatability as our newest mega act.
These looks mimic the wardrobes of her peers across the country, as if Rodrigo herself was matching prized pieces from hours of sifting through Goodwill with inspiration from a social media scroll of indie designers. In many ways, she is the cool best friend who blew up overnight.
Fashion has been elemental in Rodrigo’s ability to articulate her identity as an artist. And as a pop star born in pandemic times — growing her fan base in an entirely remote format — her particular mix of thrifted clothing and high-end vintage have helped spin a visual language that balances aspiration and approachability.
“It’s calculated in the best way; it’s more authentic to what she would wear. She cares [about how she looks] and she has to be, because of the internet. If she isn’t comfortable or doesn’t like it, we don’t even waste her time,” said Chenelle Delgadillo, who along with sister Chloe, have been Rodrigo’s stylists since the debut of her first single, “Driver’s License,” which was released in January.
And that calculation is working. “I definitely think she gives that cool friend kind of vibe — she still goes to smaller thrift shops and that’s very relatable. Sometimes you can find the best clothes so cheap, so it makes me feel like ‘OK, I could have worn that, too,’” said 18-year-old Atlanta-based mega fan Sarah Miller, who manages the Instagram account @OliviaRodrigoCloset, which documents everything Rodrigo wears. Miller founded the site in late 2019 when Rodrigo was solely known for her starring role on the Disney Channel show, “High School Musical: The Musical: The Series,” known to fans as HSMTMTS.
“Now she is using a lot of designer vintage lately and it’s something to admire from afar. I think she’s kept a lot of what I liked initially about her style, especially an interest in sustainable fashion, the same values, but she does it on a different scale now,” Miller added. As a careful observer of Rodrigo’s style, Miller says that as the singer’s fame has gotten bigger, “she is upping the ante with vintage.”
Courtesy of Petra Collins
In late June, the singer — who has yet to go on tour or reach her fans in any sizable in-person format — released a virtual concert concept on YouTube called Sour Prom, appearing in a high school gymnasium not so different than the scenes from her popular Disney television show.
Dressed in an ’80s metallic debutante dress, an oversize blazer and combat boots, the performance galvanized her identity as a teen idol for our times. Rodrigo has aimed for a new brand of pop-punk from many of her musical peers — with songs that touch on mental health and the everyday nuisances that harangue young women across the U.S., namely the toll of social media and rejection. This vulnerability has also helped endear her to audiences without ultimately connecting in real life.
Delgadillo was coy to placate any of Rodrigo’s success on her sense of style. “It is part of it but it’s just [as much] about music as about the fashion work together to create this image,” she said of the symbiosis between the two elements.
But as we have seen from the success of K-pop in international markets, including the U.S., fashion is considered to have a crucial role today in how music acts find success. Blue-chip South Korean music labels make deep investments in carefully wardrobing each of their talents. Hee Sun Choi, the stylist for girl group Itzy told WWD in 2019: “The groups that are very fashionable are more popular. Fashion is the first dimension that the audience will see visually. It’s the first mode of communication, so companies are aware of how important a group’s image and fashion is to their success.”
Rodrigo’s arrival comes in the nascent stages of Hollywood’s acceptance of vintage. While the Kardashian and Hadid clans are wearing on-trend, old designer clothes for off-duty moments, other music acts are working directly with fashion houses to wear important archival pieces on the red carpet, like Cardi B in 1995 Mugler Couture at the 2019 Grammy Awards. Harry Styles often looks like he is wearing vintage, when it is in fact vintage-inspired clothing made by Gucci. Billie Eilish notably has a wardrobe of interchangeable black vintage T-shirts.
Rodrigo, however, has a fully independent lens on vintage and thrift as it relates to high fashion — wearing it for performances, music videos and in her personal life — making impactful head-to-toe looks with old clothes that form the basis for her identity as an artist.
“She wears vintage out when she’s doing press or doing editorial shoots and I think that’s really interesting and sets her apart. It brings so much more attention to shopping secondhand and vintage,” Miller said.
So far there’s been appearances from vintage Betsey Johnson, Roberto Cavalli, Moschino, Chanel, Todd Oldham, Vivienne Westwood, Marc Jacobs and Gianni Versace, among others. They are often mixed in with a smattering of young, on-the-cusp labels like Mimi Wade, No Dress, Rachel Witus and Ashley Williams — names that you’d first hear about from your most knowing friend.
“It’s really refreshing because it’s not forced. It’s natural for Olivia because she has always been into thrift and gravitates toward more vintage. We don’t even explicitly talk about [a strategy to use vintage], it’s just how she wants to dress. It’s nice because you don’t have to worry about anyone else wearing it,” Delgadillo said.
While Chenelle works closely with archives and independent vintage stores like Aralda Vintage, where Rodrigo’s White House Chanel suit was sourced, it is Chloe who spends all night on resale sites and apps to source unique pieces. “I always wake up to a bunch of emails saying, ‘Your order is being processed,’” Delgadillo said.
And now with Rodrigo’s new music video for “Brutal,” the first song on her debut album, “Sour,” which was released in May and has steadily been at the top of U.S. music charts — the singer affirms this ideology of bringing upcycling into the entertainment mainstream. Over the last eight months, her lightning-fast trajectory to pop stardom, with magazine covers, multimillion-view social media posts and television appearances have helped to proliferate the idea of secondhand shopping as an everyday indulgence.
In her newest video, directed by Petra Collins, Rodrigo plays out different characters like a newscaster, influencer and student dressed in clothes sourced from Poshmark, eBay and Depop, along with pieces from early 2000s designer archives.
“We had fun looking back at ‘Lizzie McGuire,’ early Disney TV shows, things we grew up on like Mary-Kate and Ashley [Olsen] and seeing how random the fashion was then,” Delgadillo said of the process for “Brutal.”
In many cases, a pop act with Rodrigo’s fame would have already signed endorsement deals with fashion and cosmetic labels. But her ascent was so quick that fashion has yet to catch up. When that time comes, Delgadillo thinks Rodrigo will still be able to put her stamp on it, noting: “Yeah, she might have to wear a certain brand but that’s also cool and fun. We are always, like, ‘You are a pop star and a lot of people don’t get to wear these clothes so enjoy it for us.’ We will always throw in some smaller brands and accessories just to keep it young and fun. I think it all comes down to the styling.”
Best of WWD
Sign up for WWD's Newsletter. For the latest news, follow us on Twitter, Facebook, and Instagram.